CN116924359A - Preparation method of difluoro sulfonyl imide salt - Google Patents

Preparation method of difluoro sulfonyl imide salt Download PDF

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CN116924359A
CN116924359A CN202310653294.7A CN202310653294A CN116924359A CN 116924359 A CN116924359 A CN 116924359A CN 202310653294 A CN202310653294 A CN 202310653294A CN 116924359 A CN116924359 A CN 116924359A
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bis
reaction
imide
producing
difluoro
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张果
蔡源满
洪果
刘杜
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Jiujiang Tinci Advanced Materials Co ltd
Guangzhou Tinci Materials Technology Co Ltd
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Jiujiang Tinci Advanced Materials Co ltd
Guangzhou Tinci Materials Technology Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B21/00—Nitrogen; Compounds thereof
    • C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
    • C01B21/087—Compounds containing nitrogen and non-metals and optionally metals containing one or more hydrogen atoms
    • C01B21/093—Compounds containing nitrogen and non-metals and optionally metals containing one or more hydrogen atoms containing also one or more sulfur atoms
    • C01B21/096—Amidosulfonic acid; Salts thereof
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B21/00—Nitrogen; Compounds thereof
    • C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
    • C01B21/086—Compounds containing nitrogen and non-metals and optionally metals containing one or more sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2002/00—Crystal-structural characteristics
    • C01P2002/80—Crystal-structural characteristics defined by measured data other than those specified in group C01P2002/70
    • C01P2002/86—Crystal-structural characteristics defined by measured data other than those specified in group C01P2002/70 by NMR- or ESR-data
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
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    • Y02E60/10—Energy storage using batteries

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Abstract

The invention belongs to the technical field of lithium ion battery materials, and discloses a preparation method of difluoro sulfonyl imide salt. The preparation method comprises the following steps: adding phosgene, diphosgene or triphosgene, sulfamic acid and chlorosulfonic acid into a reactor, mixing, and heating for reaction to obtain a mixture; rectifying the obtained mixture under reduced pressure to obtain dichloro sulfonyl imide; adding the obtained bis (chlorosulfonyl) imide into a reactor, and adding anhydrous HF (hydrogen fluoride) under the stirring condition for mixing reaction to obtain bis (fluorosulfonyl) imide; under the condition of isolating moisture, the obtained difluoro sulfimide is mixed with an alkali metal source for reaction, and the product is separated and purified to obtain the difluoro sulfimide salt. The method adopts phosgene, diphosgene or triphosgene to replace common thionyl chloride to prepare HCSI, and prepares the difluoro sulfimide salt through fluorination and salifying, thereby improving the safety of the preparation process and reducing the production of toxic byproducts. Meanwhile, the production cost is obviously reduced and the method is more suitable for industrial production.

Description

Preparation method of difluoro sulfonyl imide salt
Technical Field
The invention belongs to the technical field of lithium ion battery materials, and particularly relates to a preparation method of difluoro sulfonyl imide salt.
Background
Bischlorosulfonimide ((SO) 2 Cl) 2 NH, HCSI) and bis-fluorosulfonyl imide ((SO) 2 F) 2 The NH and HFSI are two substances which are lithium bis (fluorosulfonyl) imide additives for lithium salt of synthetic lithium ion batteries (the chemical formula is LiN (SO) 2 F) 2 Abbreviated as LiFSI). LiFSI has a specific LiPF 6 Better heat stability and conductivity, is a better electrolyte lithium salt, is mainly used as electrolyte additive at present, and is expected to replace LiPF 6 . And with the development of battery technology, other alkali metal bis (fluorosulfonyl) imide salts have wide application prospects.
The main preparation method of the difluoro sulfonyl imide salt is as follows: appelet al,1962,95,1753, M.Beranetal, Z.Anorg.Allg.Chem.2005,631,55, US4315935, CN102786452, etc. disclose synthesis of HCSI from chlorosulfonic acid, thionyl chloride and sulfamic acid, followed by fluorination with a fluorinating agent to obtain HFSI, which is reacted with a lithium compound to prepare LiFSI. The method has the advantages of easily available raw materials, low cost, more harmful acid gases, high risk of raw material thionyl chloride, sensitivity to water and easy decomposition. US8337797, US9156692, US5916475 and Inorg. Synth.11,138-143 (1968) disclose urea (CO (NH) 2 ) 2 ) With fluorosulfonic acid (FSO) 3 H) Process for preparing HFSI by mixed heating reaction, HFSI produced and FSO added in excess 3 H can be recovered by distillation under reduced pressure. Wherein US8337797 discloses that the yield of urea standard of the obtained product HFSI is about 40% by adopting a Polytetrafluoroethylene (PTFE) material reactor, the reaction temperature is 120-130 ℃. FSO used in the method 3 H is expensive and requires high equipment, resulting in very high costs. In addition, the process has low yields and FSO 3 H has very close boiling points to HFSI and is difficult to separate.
Patent CN109786248A discloses a method for preparing HFSI organic base salt by using sulfuryl fluoride and ammonium fluoride, triethylamine in an organic solvent, then reacting with strong acid, and obtaining HFSI by distillation. Although the yield of the method can be improved to 90%, the method can cause a plurality of impurities and difficult treatment of byproducts because of the organic base used in the method.
Patent CN106044728A discloses a method for preparing dichlorsulfonylimide by reacting chlorosulfonyl isocyanate with chlorosulfonic acid, and preparing LiFSI by fluorination and salification. The method avoids the use of sulfamic acid, and the homogeneous reaction is easier to control. However, the raw material chlorosulfonyl isocyanate is expensive and difficult to supply, and greatly limits the industrialized application.
Patent CN115028146a discloses a preparation method of sodium difluorosulfimide, which adopts sulfamic acid, fluorosulfonic acid and carbonyl fluoride gas to prepare the difluorosulfimide through one-step reaction. However, the method has the problems of difficult acquisition of raw materials of fluorosulfonic acid and carbonyl fluoride, high price and high cost. Especially, the fluorosulfonic acid has the capacity of large-scale production in China at present, and the industrialization application is greatly limited.
Disclosure of Invention
In view of the above drawbacks and shortcomings of the prior art, an object of the present invention is to provide a process for the preparation of bis-fluorosulfonyl imide salts. The method adopts phosgene (carbonyl chloride), diphosgene (trichloromethyl chloroformate) or triphosgene (di (trichloromethyl) carbonate) to replace common thionyl chloride to prepare HCSI, and prepares the difluoro sulfimide salt through fluorination and salification, thereby improving the safety of the preparation process and reducing the generation of toxic byproducts. Meanwhile, the production cost is obviously reduced and the method is more suitable for industrial production.
The invention aims at realizing the following technical scheme:
a method for preparing bis-fluorosulfonyl imide salt, comprising the following steps:
(1) Adding sulfamic acid and chlorosulfonic acid into a reactor, mixing, heating to 50-60 ℃, introducing phosgene, stopping introducing when the solid sulfamic acid is completely reacted and dissolved until the reaction solution is clear, heating to 70-130 ℃, reacting at a constant temperature, and discharging gas to obtain a mixture; or, adding sulfamic acid and chlorosulfonic acid into a reactor, adding diphosgene or triphosgene, mixing, heating to 70-120 ℃ and reacting at a constant temperature to obtain a mixture; rectifying the obtained mixture under reduced pressure to obtain dichloro sulfonyl imide;
(2) Adding the dichlorsulfimide obtained in the step (1) into a reactor, and adding anhydrous HF (hydrogen fluoride) under the stirring condition for mixing reaction to obtain the dichlorsulfimide;
(3) And (3) under the condition of isolating moisture, mixing and reacting the difluoro sulfimide obtained in the step (2) with an alkali metal source, and separating and purifying a product to obtain the difluoro sulfimide salt.
Further, the molar ratio of sulfamic acid, chlorosulfonic acid and phosgene in the step (1) is preferably (1-1.1): 1 (2-3); the molar ratio of sulfamic acid, chlorosulfonic acid and diphosgene is preferably (1-1.1): 1 (1-1.2); the molar ratio of sulfamic acid, chlorosulfonic acid and triphosgene is preferably 1 to 1.1:1 (0.67 to 1).
Further, the time for introducing phosgene in the step (1) is preferably 0.5 to 4 hours.
Further, the time of the incubation reaction in step (1) is preferably 3 to 6 hours.
Further, the molar ratio of the bischlorosulfonimide to the HF in the step (2) is preferably 1 (1-2).
Further, the temperature of the mixing reaction in the step (2) is preferably 10 to 120 ℃, and the time of the mixing reaction is preferably 4 to 8 hours.
Further, the bisfluorosulfonyl imide obtained in the step (2) is further purified by distillation or rectification.
Further, the alkali metal source in step (3) includes, but is not limited to, simple substances, halogenated salts, acid salts, hydroxides, and the like of alkali metals.
Further, the molar ratio of the bisfluorosulfonyl imide to the alkali metal source in the step (3) is preferably 1 (1 to 1.3).
Further, the temperature of the mixing reaction in the step (3) is preferably 20 to 150 ℃.
Further, the mixed reaction of the bisfluorosulfonyl imide and the alkali metal source in the step (3) is performed under the condition of an organic good solvent, wherein the organic good solvent is selected from one or more than two solvents selected from acetonitrile, methyl ethyl carbonate, dimethyl carbonate, diethyl carbonate, ethylene carbonate, propylene carbonate, ethyl acetate, methyl acetate, propyl acetate, isopropyl acetate, butyl acetate, ethylene glycol dimethyl ether, ethylene glycol diisodiethyl ether, diethylene glycol dimethyl ether, acetone, tetrahydrofuran, methyltetrahydrofuran, diethyl ether, propyl ether, butyl ether, anisole, diphenyl ether, 1, 4-dioxane and the like.
Further, the separation and purification step in the step (3) comprises filtration, concentration, crystallization or washing by adding a poor solvent, solid-liquid separation and drying; the poor solvent is selected from one or more than two solvents selected from toluene, xylene, chlorobenzene, dichlorobenzene, trichlorobenzene, tetrachlorobenzene, dichloromethane, trichloromethane, tetrachloromethane, dichloroethane, trichloroethane, tetrachloroethane and the like.
The reaction formula of the invention is as follows:
compared with the prior art, the invention has the beneficial effects that:
the preparation method adopts phosgene (carbonyl chloride), diphosgene (trichloromethyl chloroformate) or triphosgene (di (trichloromethyl) carbonate) to replace common thionyl chloride to prepare HCSI, and prepares the difluoro-sulfonyl imide salt through fluorination and salification. The used raw materials, especially diphosgene and triphosgene, are more stable, so that the safety of the preparation process can be improved, and the generation of toxic byproduct sulfur dioxide is avoided.
Drawings
FIG. 1 is an F-NMR spectrum of bis-fluorosulfonyl imide obtained in example 1;
FIG. 2 is an F-NMR spectrum of a lithium bis-fluorosulfonyl imide product obtained in example 1;
FIG. 3 is an F-NMR spectrum of a sodium difluorosulfimide product obtained in example 5.
Detailed Description
The present invention will be described in further detail with reference to examples and drawings, but embodiments of the present invention are not limited thereto.
Example 1
(1) Preparation of bischlorosulfimide:
50g of sulfamic acid and 60g of chlorosulfonic acid are added into a 500mL reaction bottle, heated to 50-60 ℃ after being mixed, 101.9g of phosgene is introduced in 2h, the temperature of the reactant is raised to 110 ℃ after being clarified, the reaction is carried out for 5h, and colorless transparent liquid is obtained after reduced pressure distillation, namely 101.5g of dichlorosulfimide, and the yield is 92.1%.
(2) Preparation of bis (fluorosulfonyl) imide:
100g of the dichloro-sulphonyl-imide prepared in the step (1) is added into a 500mL tetrafluoro reaction bottle, the temperature is raised to 100 ℃, HF gas is slowly introduced into the bottle under stirring for about 14g, the reaction time is reduced to room temperature after 6h, nitrogen is blown for 2h, about 82g of crude product is obtained, 74.35g of colorless liquid is obtained through reduced pressure distillation, and the yield is 87.9%. The F-NMR spectrum of the obtained bis-fluorosulfonyl imide is shown in FIG. 1.
(3) Preparation of lithium bis (fluorosulfonyl) imide:
in a 500mL tetrafluoro reaction bottle, adding 12g of lithium chloride and 150g of acetonitrile to prepare a mixed solution, dropwise adding 50g of the difluoro sulfonimide prepared in the step (2), reacting for 2 hours at 25 ℃, filtering to remove unreacted lithium chloride, concentrating to obtain a viscous liquid, adding dichloromethane to separate out crystals, filtering, and drying a filter cake at 40 ℃ under reduced pressure to obtain 49.7g of difluoro sulfonimide lithium product with a yield of 96.21%. The F-NMR spectrum of the obtained lithium bis (fluorosulfonyl) imide product is shown in FIG. 2.
Example 2
(1) Preparation of bischlorosulfimide:
55g of sulfamic acid and 60g of chlorosulfonic acid are added into a 500mL reaction bottle, heated to 50-60 ℃ after mixing, 152g of phosgene is introduced in 2h, the temperature of the reactants is raised to 80 ℃ after clarification, the reaction is carried out for 6h, and colorless transparent liquid is obtained after reduced pressure distillation, namely 102.6g of dichlorosulfimide, and the yield is 93.1%.
(2) Preparation of bis (fluorosulfonyl) imide:
100g of the dichloro-sulphonyl-imide prepared in the step (1) is added into a 500mL tetrafluoro reaction bottle, the temperature is raised to 80 ℃, HF gas is slowly introduced into the bottle under stirring for about 10g, the reaction time is reduced to room temperature after 8h, nitrogen is blown for 2h, about 83g of crude product is obtained, 73.52g of colorless liquid is obtained through reduced pressure distillation, and the yield is 86.9%.
(3) Preparation of lithium bis (fluorosulfonyl) imide:
13g of lithium chloride and 150g of methyl ethyl carbonate are added into a 500mL tetrafluoro reaction bottle to prepare a mixed solution, 50g of the difluoro sulfonimide prepared in the step (2) is added dropwise, unreacted lithium chloride is removed by filtration after reacting for 2 hours at 50 ℃, a viscous liquid is obtained by concentration, dichloroethane is added to precipitate crystals, filtration and decompression drying of a filter cake at 40 ℃ are carried out, and 50.1g of difluoro sulfonimide lithium product is obtained, and the yield is 97.0%.
Example 3
(1) Preparation of bischlorosulfimide:
102g of diphosgene, 50g of sulfamic acid and 60g of chlorosulfonic acid are added into a 500mL reaction bottle, are heated to 120 ℃ for reaction for 5 hours, and are distilled under reduced pressure to obtain colorless transparent liquid, namely 95.22g of dichlor sulfimide, and the yield is 86.4%.
(2) Preparation of bis (fluorosulfonyl) imide:
90g of the crude dichloro-sulphonyl-imine product obtained in the step (1) is added into a 500mL tetrafluoro reaction bottle, the temperature is raised to 100 ℃, HF gas is slowly introduced into the bottle under stirring for about 12.6g, the temperature is reduced to room temperature after the reaction for 6h, nitrogen is blown for 2h, about 75g of the crude product is obtained, and 66.75g of colorless liquid is obtained through reduced pressure distillation, and the yield is 87.69%.
(3) Preparation of lithium bis (fluorosulfonyl) imide:
7.2g of lithium fluoride and 150g of methyl ethyl carbonate are added into a 500mL tetrafluoro reaction bottle to prepare a mixed solution, 50g of the difluoro sulfonimide prepared in the step (2) is added dropwise, unreacted lithium fluoride is removed by filtration after reacting for 2 hours at 50 ℃, thick liquid is obtained by concentration, toluene is added to precipitate crystals, filtration and decompression drying of a filter cake at 50 ℃ are carried out, and 48.2g of difluoro sulfonimide lithium product is obtained, and the yield is 93.3%.
Example 4
(1) Preparation of bischlorosulfimide:
122g of diphosgene, 55g of sulfamic acid and 60g of chlorosulfonic acid are added into a 500mL reaction bottle, are mixed, are heated to 90 ℃ for reaction for 6 hours, and are distilled under reduced pressure to obtain colorless transparent liquid, namely 96.40g of dichlor sulfimide, and the yield is 87.5%.
(2) Preparation of bis (fluorosulfonyl) imide:
90g of the crude dichloro-sulphonyl-imine product obtained in the step (1) is added into a 500mL tetrafluoro reaction bottle, the temperature is raised to 90 ℃, HF gas is slowly introduced into the bottle under stirring for about 15g, the reaction time is reduced to room temperature after 6h, nitrogen is blown for 2h, about 78g of the crude product is obtained, 67.24g of colorless liquid is obtained through reduced pressure distillation, and the yield is 88.33%.
(3) Preparation of lithium bis (fluorosulfonyl) imide:
adding 9.3g of lithium fluoride and 150g of dimethyl carbonate into a 500mL tetrafluoro reaction bottle to prepare a mixed solution, dropwise adding 50g of the difluoro sulfonimide prepared in the step (2), reacting for 1h at 80 ℃, filtering to remove unreacted lithium fluoride, concentrating to obtain a viscous liquid, adding xylene to separate out crystals, filtering, and drying a filter cake at 50 ℃ under reduced pressure to obtain 48.5g of difluoro sulfonimide lithium product with the yield of 93.8%.
Example 5
(1) Preparation of bischlorosulfimide:
102g of triphosgene, 50g of sulfamic acid and 60g of chlorosulfonic acid are added into a 500mL reaction bottle, mixed and heated to 80-85 ℃ to enable the triphosgene to be completely melted, and after 3h of reaction, the temperature is raised to 120 ℃ and the reaction is kept for 3h. Distillation under reduced pressure gave 96.37g of dichlorosulfimide as a colorless transparent liquid in a yield of 87.44%.
(2) Preparation of bis (fluorosulfonyl) imide:
the procedure is as in example 1 with a yield of 88.01%.
(3) Preparation of sodium bis (fluorosulfonyl) imide:
adding 12.18g of sodium fluoride and 150g of dimethyl carbonate into a 500mL tetrafluoro reaction bottle to prepare a mixed solution, dropwise adding 50g of the difluoro sulfimide prepared in the step (2), reacting for 2 hours at 50 ℃, filtering to remove unreacted sodium fluoride, concentrating under reduced pressure at 40 ℃ to obtain a solid crude product, adding dichloromethane to wash the crude product, filtering, and drying the filter cake under reduced pressure at 50 ℃ to obtain 54.07g of difluoro sulfimide sodium product with a yield of 96.42%. The F-NMR spectrum of the obtained sodium difluorosulfimide product is shown in FIG. 3.
The above embodiments are preferred embodiments of the present invention, but the embodiments of the present invention are not limited to the above embodiments, and any other modifications, substitutions, combinations, and simplifications without departing from the spirit and principles of the present invention should be made in the equivalent manner, and all the modifications, substitutions, combinations, and simplifications should be included in the scope of the present invention.

Claims (10)

1. A method for preparing a bis-fluorosulfonyl imide salt, which is characterized by comprising the following preparation steps:
(1) Adding sulfamic acid and chlorosulfonic acid into a reactor, mixing, heating to 50-60 ℃, introducing phosgene, stopping introducing when the solid sulfamic acid is completely reacted and dissolved until the reaction solution is clear, heating to 70-130 ℃, reacting at a constant temperature, and discharging gas to obtain a mixture; or, adding sulfamic acid and chlorosulfonic acid into a reactor, adding diphosgene or triphosgene, mixing, heating to 70-120 ℃ and reacting at a constant temperature to obtain a mixture; rectifying the obtained mixture under reduced pressure to obtain dichloro sulfonyl imide;
(2) Adding the dichlorsulfimide obtained in the step (1) into a reactor, and adding anhydrous HF (hydrogen fluoride) under the stirring condition for mixing reaction to obtain the dichlorsulfimide;
(3) And (3) under the condition of isolating moisture, mixing and reacting the difluoro sulfimide obtained in the step (2) with an alkali metal source, and separating and purifying a product to obtain the difluoro sulfimide salt.
2. The process for producing a difluorosulfinamide salt according to claim 1, wherein the molar ratio of sulfamic acid, chlorosulfonic acid and phosgene in step (1) is 1 to 1.1, 1 to 3; the mol ratio of sulfamic acid, chlorosulfonic acid and diphosgene is (1-1.1): 1 (1-1.2); the mol ratio of sulfamic acid, chlorosulfonic acid and triphosgene is (1-1.1): 1 (0.67-1).
3. The method for producing a bis-fluorosulfonyl imide salt according to claim 1, wherein the time for introducing phosgene in step (1) is 0.5 to 4 hours; the time of the heat preservation reaction is 3-6 h.
4. The process for producing a bis-fluorosulfonyl imide salt according to claim 1, wherein the molar ratio of the bis-chlorosulfonyl imide to HF in the step (2) is 1 (1-2).
5. The method for producing a bis-fluorosulfonyl imide salt according to claim 1, wherein the temperature of the mixing reaction in the step (2) is 10 to 120 ℃, and the time of the mixing reaction is 4 to 8 hours.
6. The process for producing a difluorosulfimide salt according to claim 1, wherein the difluorosulfimide obtained in the step (2) is further purified by distillation or rectification.
7. A process for the preparation of bis-fluorosulfonyl imide salts as claimed in claim 1 wherein the alkali metal source in step (3) comprises an elemental, halogenated, acid or hydroxide salt of an alkali metal.
8. The process for producing a bis-fluorosulfonyl imide salt according to claim 1, wherein the molar ratio of the bis-fluorosulfonyl imide to the alkali metal source in step (3) is 1 (1-1.3).
9. The method for producing a bis-fluorosulfonyl imide salt according to claim 1, wherein the temperature of the mixing reaction in step (3) is 20 to 150 ℃; the mixed reaction of the difluoro sulfimide and the alkali metal source is carried out under the condition of an organic good solvent, wherein the organic good solvent is selected from one or more than two solvents of acetonitrile, methyl ethyl carbonate, dimethyl carbonate, diethyl carbonate, ethylene carbonate, propylene carbonate, ethyl acetate, methyl acetate, propyl acetate, isopropyl acetate, butyl acetate, ethylene glycol dimethyl ether, ethylene glycol diisodiethyl ether, diethylene glycol dimethyl ether, acetone, tetrahydrofuran, methyltetrahydrofuran, diethyl ether, propyl ether, butyl ether, anisole, diphenyl ether and 1, 4-dioxane.
10. The method for producing a bis-fluorosulfonyl imide salt according to claim 1, wherein the separation and purification step in step (3) comprises filtration, concentration, crystallization or washing with a poor solvent, solid-liquid separation and drying; the poor solvent is selected from one or more than two solvents selected from toluene, xylene, chlorobenzene, dichlorobenzene, trichlorobenzene, tetrachlorobenzene, dichloromethane, trichloromethane, tetrachloromethane, dichloroethane, trichloroethane and tetrachloroethane.
CN202310653294.7A 2023-06-05 2023-06-05 Preparation method of difluoro sulfonyl imide salt Pending CN116924359A (en)

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